US2932647A - Thioformal and acetal derivatives of mercaptopyridine-1-oxide - Google Patents
Thioformal and acetal derivatives of mercaptopyridine-1-oxide Download PDFInfo
- Publication number
- US2932647A US2932647A US757201A US75720158A US2932647A US 2932647 A US2932647 A US 2932647A US 757201 A US757201 A US 757201A US 75720158 A US75720158 A US 75720158A US 2932647 A US2932647 A US 2932647A
- Authority
- US
- United States
- Prior art keywords
- oxide
- mercaptopyridine
- pyridyl
- percent
- alpha
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- -1 acetal derivatives of mercaptopyridine-1-oxide Chemical class 0.000 title description 9
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 16
- 238000000034 method Methods 0.000 description 13
- 241000233866 Fungi Species 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000417 fungicide Substances 0.000 description 6
- 159000000000 sodium salts Chemical class 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- YBBJKCMMCRQZMA-UHFFFAOYSA-N pyrithione Chemical class ON1C=CC=CC1=S YBBJKCMMCRQZMA-UHFFFAOYSA-N 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 239000003429 antifungal agent Substances 0.000 description 2
- 229940121375 antifungal agent Drugs 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 230000000881 depressing effect Effects 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- FGVVTMRZYROCTH-UHFFFAOYSA-N pyridine-2-thiol N-oxide Chemical compound [O-][N+]1=CC=CC=C1S FGVVTMRZYROCTH-UHFFFAOYSA-N 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- KIRLBCKNLVOUDA-UHFFFAOYSA-N 1-(chloromethoxy)dodecane Chemical compound CCCCCCCCCCCCOCCl KIRLBCKNLVOUDA-UHFFFAOYSA-N 0.000 description 1
- DVHSGCVPLAYGIF-UHFFFAOYSA-N 1-(chloromethoxy)octadecane Chemical compound CCCCCCCCCCCCCCCCCCOCCl DVHSGCVPLAYGIF-UHFFFAOYSA-N 0.000 description 1
- VHUQXPJHMISKGS-UHFFFAOYSA-N 1-(chloromethoxy)propane Chemical compound CCCOCCl VHUQXPJHMISKGS-UHFFFAOYSA-N 0.000 description 1
- GSGPUGZLDGHFDO-UHFFFAOYSA-N 2-(chloromethoxy)propane Chemical compound CC(C)OCCl GSGPUGZLDGHFDO-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 241001530056 Athelia rolfsii Species 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000223218 Fusarium Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 241000233614 Phytophthora Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000233639 Pythium Species 0.000 description 1
- 241000813090 Rhizoctonia solani Species 0.000 description 1
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000187181 Streptomyces scabiei Species 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 241000082085 Verticillium <Phyllachorales> Species 0.000 description 1
- VSYMNDBTCKIDLT-UHFFFAOYSA-N [2-(carbamoyloxymethyl)-2-ethylbutyl] carbamate Chemical compound NC(=O)OCC(CC)(CC)COC(N)=O VSYMNDBTCKIDLT-UHFFFAOYSA-N 0.000 description 1
- XOCUXOWLYLLJLV-UHFFFAOYSA-N [O].[S] Chemical compound [O].[S] XOCUXOWLYLLJLV-UHFFFAOYSA-N 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 125000006278 bromobenzyl group Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- JWMLCCRPDOIBAV-UHFFFAOYSA-N chloro(methylsulfanyl)methane Chemical compound CSCCl JWMLCCRPDOIBAV-UHFFFAOYSA-N 0.000 description 1
- FCYRSDMGOLYDHL-UHFFFAOYSA-N chloromethoxyethane Chemical compound CCOCCl FCYRSDMGOLYDHL-UHFFFAOYSA-N 0.000 description 1
- STZUMARNGFQGPH-UHFFFAOYSA-N chloromethoxyethene Chemical compound ClCOC=C STZUMARNGFQGPH-UHFFFAOYSA-N 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 244000053095 fungal pathogen Species 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 150000004250 monothioacetals Chemical class 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 230000000590 parasiticidal effect Effects 0.000 description 1
- 239000002297 parasiticide Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000001965 potato dextrose agar Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229940045998 sodium isethionate Drugs 0.000 description 1
- LADXKQRVAFSPTR-UHFFFAOYSA-M sodium;2-hydroxyethanesulfonate Chemical compound [Na+].OCCS([O-])(=O)=O LADXKQRVAFSPTR-UHFFFAOYSA-M 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
Definitions
- hydrohalide salts of this invention can thus be prepared in good yield.
- Benzene is the preferred medium for this reaction but other inert organic solvents, for example, ethylene dichloride can be used.
- Any hydroh-alide salt can be prepared but the hydrochlorides and hydrobromides are particularly pre- RAH+CH O +HC1 RACH2Ci+H2O in which R and A are defined before.
- the re- 111 Whlch A 18 Oxygen Sulfur; R 13 hydrogen, y sultant alpha-chloroethers or thioethers can be employed Carbon halohydlocalbon radical, especlally an alkyl, for the preparation of a mono or dithioformal or acetal alkenyl, alicyclic or aryl radical containing 1 to 18 carbon according to the process herein described. atoms and is y g a lower f l y g P or a halo-
- u pyridinei-oxide to form them, and radicals R and R are The 2-pyr1dyl-1-ox1de radical, C H4N(- 'O)S ill the shown in the following table:
- Reagent A R Product 0 H N 0 SCH OH GHO+HOI 0 i%-ig%rzci?yggestgfil 2s-ngcaptopyridine-l-oxide.
- R can also be beta,beta-dichloroethyl, the structural formulas: isopropyl and n-amyl or other lower alkyl or halogenated 60 lower alkyl group containing 1 to 5 carbon atoms.
- the compounds of this invention are useful in diluted
- the compounds of this invention are prepared by the compositions as pesticides.
- CsHt R c compounds are used advantageously in a proportion of where M is a suitable cation, e.g., a metal or a positive about 15 to 18 percent with any of the dlluents usually radical, for example, hydrogen, sodium, potassium, am employed for the application of foliar fungicides or for monium or substituted ammonium.
- A, R, R are as deapplication to the soil where they control the activ ty of fined above. This reaction occurs readily and can be soil fungi.
- the compounds of this nvention are o1ls or carried out in a variety of. reaction media, although crystalline solids and are suitably dispersed on an m ertacetone or dioxane as.
- the reaction medium is preferredfinely divided solid and employed as a dust. Suitable when a salt ofZ-mercaptopyridinethione is used. solid carriers are clay, talc, bentonite, as well as other Alternatively, the reaction can be carried out by employing 2-mercaptopyridine-l-oxide as a free acid in a carriers known in the art. (See Frear, Chemistry of Insecticides, Fungicides and Herbicides) Microcel 805,
- a synthetic calcium silicate is an example of a suitable solid carrier.
- the compounds may also be applied as a spray in a liquid carrier either as a solution in a solvent or as asuspension ina non-solvent for example, water.
- Marasperse N is a suitable dispersant of the lignosulfonate type.
- Igepon AP7 8 an ester of sodium isethionate, is a suitable wetting agent.
- the proportion of dispersant is suitably from about 1 to 3 percent and the wetting agent is suitably from about 2 to 10 percent of the composition.
- the compounds of this invention may also be admixed with carriers that are themselves active, such as other parasiticides, herbicides I and fertilizers.
- Tests as soil fungicides were carried out by placing discs of agar cultures 5 mm. in diameter of the pathogenic fungi listed in the table below on Petri dish plates of potato dextrose agar containing 10, 100 and 1000 parts per million, respectively, of the chemical being tested The plates were then incubated for 48 hours at 20 C. to give satisfactory growth of the fungi on control plates containing no chemical.
- the growth of the fungi on the test plates was then observed and noted as 0 for no growth, indicated a kill of the fungi; for grown of the original inoeulum only, indicating a decided depressing etfect of fungus growth but no of the fungus and indicating no inhibition of fungal growth and, therefore, no pronounced depressing eifect of the chemical being tested.
- Test Organism I B-(Z-pyridyl-l-oxide) O-methyl monothioiormal, p.p.m. Test Organism I These data show complete control of all of the several fungi tested at 1000 parts per million, nearly complete control at 100 p.p.m. and partial control with as low as l0 p.p.m. of this anti-fungal agent.
- EXAMPLE XI S-(Z-pyridyZ-l-oxide) 'S-n-prapyl dithioformal hydrochloride Following the procedure of Example X, Z-mercaptopyridine-l-oxide was treated with chloromethyl npropyl sulfide.
- a process for the preparation of a compound according to claim 1 which comprises reacting a 2-mercaptopyridine-l-oxide compound with a compound selected from the group consisting of alpha-halothioether and alpha-haloether.
- a process for the preparation of a compound according to claim 1 which comprises reacting a salt of Z-mercaptopyridine-l-oxide with a compound selected from the group consisting of alpha-chlorothioether and alpha-chloroether.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL108061D NL108061C (en, 2012) | 1958-08-26 | ||
| BE581827D BE581827A (en, 2012) | 1958-08-26 | ||
| NL242639D NL242639A (en, 2012) | 1958-08-26 | ||
| US757201A US2932647A (en) | 1958-08-26 | 1958-08-26 | Thioformal and acetal derivatives of mercaptopyridine-1-oxide |
| GB25903/59A GB908638A (en) | 1958-08-26 | 1959-07-28 | 2-pyridyl-1-oxido thio ethers, their manufacture and pesticidal compositions thereof |
| FR802595A FR1235741A (fr) | 1958-08-26 | 1959-08-11 | Obtention de dérivés mono-et dithioformal et acétal de 2-mercaptopyridine-1-oxyde |
| DEO6920A DE1193944B (de) | 1958-08-26 | 1959-08-13 | Verfahren zur Herstellung von 2-Mercapto-pyridin-1-oxydderivaten |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US757201A US2932647A (en) | 1958-08-26 | 1958-08-26 | Thioformal and acetal derivatives of mercaptopyridine-1-oxide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2932647A true US2932647A (en) | 1960-04-12 |
Family
ID=25046817
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US757201A Expired - Lifetime US2932647A (en) | 1958-08-26 | 1958-08-26 | Thioformal and acetal derivatives of mercaptopyridine-1-oxide |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US2932647A (en, 2012) |
| BE (1) | BE581827A (en, 2012) |
| DE (1) | DE1193944B (en, 2012) |
| FR (1) | FR1235741A (en, 2012) |
| GB (1) | GB908638A (en, 2012) |
| NL (2) | NL242639A (en, 2012) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3155671A (en) * | 1962-03-19 | 1964-11-03 | Monsanto Co | Benzyl thiopyridine oxides |
| US3207760A (en) * | 1962-04-10 | 1965-09-21 | S B Penick & Company | S-(2-pyridyl-1-oxide)-thioarylates |
| US3295946A (en) * | 1962-03-19 | 1967-01-03 | Monsanto Co | Controlling vegetation with benzyl thiopyridine oxides |
| US3674877A (en) * | 1970-06-02 | 1972-07-04 | Ici Ltd | Pesticidally active compounds and compositions containing them |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2686786A (en) * | 1953-01-09 | 1954-08-17 | Olin Mathieson | Nu-hydroxy-2-pyridinethiones and method of preparing same |
| US2734903A (en) * | 1956-02-14 | Thiocyanic esters of pyridine oxides |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2742476A (en) * | 1953-10-26 | 1956-04-17 | Olin Mathieson | Derivatives of 2-mercaptopyridine 1-oxide |
-
0
- BE BE581827D patent/BE581827A/xx unknown
- NL NL108061D patent/NL108061C/xx active
- NL NL242639D patent/NL242639A/xx unknown
-
1958
- 1958-08-26 US US757201A patent/US2932647A/en not_active Expired - Lifetime
-
1959
- 1959-07-28 GB GB25903/59A patent/GB908638A/en not_active Expired
- 1959-08-11 FR FR802595A patent/FR1235741A/fr not_active Expired
- 1959-08-13 DE DEO6920A patent/DE1193944B/de active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2734903A (en) * | 1956-02-14 | Thiocyanic esters of pyridine oxides | ||
| US2686786A (en) * | 1953-01-09 | 1954-08-17 | Olin Mathieson | Nu-hydroxy-2-pyridinethiones and method of preparing same |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3155671A (en) * | 1962-03-19 | 1964-11-03 | Monsanto Co | Benzyl thiopyridine oxides |
| US3295946A (en) * | 1962-03-19 | 1967-01-03 | Monsanto Co | Controlling vegetation with benzyl thiopyridine oxides |
| US3207760A (en) * | 1962-04-10 | 1965-09-21 | S B Penick & Company | S-(2-pyridyl-1-oxide)-thioarylates |
| US3674877A (en) * | 1970-06-02 | 1972-07-04 | Ici Ltd | Pesticidally active compounds and compositions containing them |
Also Published As
| Publication number | Publication date |
|---|---|
| GB908638A (en) | 1962-10-24 |
| NL242639A (en, 2012) | |
| FR1235741A (fr) | 1960-07-08 |
| NL108061C (en, 2012) | |
| DE1193944B (de) | 1965-06-03 |
| BE581827A (en, 2012) |
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